Organic chemistry – 14.3 Bonding: structural formulas

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Bonding Structural formulas Outline
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Saturation Degree of saturation
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Bonding Structural formulas Saturation Outline
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Term: saturated Term: unsaturated Concept: saturated compound Concept: unsaturated compound
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Bonding Structural formulas Saturation Term: saturated
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– Contains no pi bonds – no rings
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Bonding Structural formulas Saturation Term: unsaturated
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– contains at least one pi bond or a ring
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Bonding Structural formulas Saturation n
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carbon
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Bonding Structural formulas Saturation Concept: saturated compound
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A saturated compound with n carbon atoms has exactly 2n+2 hydrogen atoms
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Bonding Structural formulas Saturation Concept: unsaturated compound
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A unsaturated compound with n carbon atoms has fewer than 2n+2 hydrogens.
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Bonding Structural formulas Degree of unsaturation of simple organic molecules Outline
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d Formula of degree of unsaturation Formula of degree of unsaturation: n Formula of degree of unsaturation: x Formula of degree of unsaturation: x (other atoms) Degree of unsaturation and hybrid bonds Examples
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Bonding Structural formulas Degree of unsaturation of simple organic molecules d
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degree of unsaturation
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Bonding Structural formulas Degree of unsaturation of simple organic molecules Formula of degree of unsaturation
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((2n+2)-x)/2
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Bonding Structural formulas Degree of unsaturation of simple organic molecules Formula of degree of unsaturation: n
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carbons
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Bonding Structural formulas Degree of unsaturation of simple organic molecules Formula of degree of unsaturation: x
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hydrogens
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Bonding Structural formulas Degree of unsaturation of simple organic molecules Formula of degree of unsaturation: x (other atoms)
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x represents the number of hydrogens and any monovalent atoms
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Bonding Structural formulas Degree of unsaturation of simple organic molecules Formula of degree of unsaturation: x (monovalent atoms)
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Such as halogens: F Cl Br I
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Bonding Structural formulas Degree of unsaturation of simple organic molecules Formula of degree of unsaturation: x (oxygen)
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Since the number of oxygens has no effect, it is ignored.
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Bonding Structural formulas Degree of unsaturation of simple organic molecules Formula of degree of unsaturation: x (nitrogen)
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for nitrogen-containing compounds, replacing each N by 1 C and 1 H when using this formula.
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Bonding Structural formulas Degree of unsaturation of simple organic molecules Degree of unsaturation and hybrid bonds Indication: one degree of unsaturation
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One degree of unsaturation: presence of – one pi bond or -one ring
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Bonding Structural formulas Degree of unsaturation of simple organic molecules Degree of unsaturation and hybrid bonds Indication: two degrees of unsaturation
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Possibilites: – two bi bonds (two separate double bonds or one triple bond), or – one pi bond and one ring or – two rings and so on.
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Bonding Structural formulas Degree of unsaturation of simple organic molecules Degree of unsaturation and hybrid bonds Example: one degree of unsaturation 4-Chlorobutene (C4H7Cl)
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– 4 carbon, 7 hydrogen – Number of hydrogen is different. – each halogen atom (F, Cl, B, I) or other monovalent atom “replaces” one hydrogen atom, so d= ((2.4+2)-(7-1))/2=1
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Bonding Structural formulas Degree of unsaturation of simple organic molecules Formula divalent atom
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replace one carbon and two hydrogen atoms
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Bonding Structural formulas Degree of unsaturation of simple organic molecules Degree of unsaturation and hybrid bonds example: one degree of unsaturation Methoxyethene (C3H6O)
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– 3 carbons, 6 hydrogen – each oxygen (or other divalent atom) replaces one carbon and two hydrogen atoms. – CH2 groups are sometimes referred to as methylene groups so d= ((2(3+1)+2)-(6+2))/2=1 – Since a divalent atom can take the place of a methylene group, it does not affect the degree of unsaturation, and can be ignored.

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